Isopropylamine → (E)(E) 2,7-bis-(5-hydroxy-3-methyl-pent-3-en-1-ynyl)-fluoren-9-one

Participants

Reaction Steps

To a solution of 2,7-dibromo-9-fluorenone (338 mg, 1.0 mmol) in dry THF (17 mL) under a nitrogen atmosphere were added copper(I) iodide (30 mg, 0.16 mmol) and dichlorobis(triphenylphosphine)palladium (II) (70 mg, 0.10 mmol), trans-3-methyl-2-penten-4-yn-1-ol (481 mg, 5.0 mmol) and dry isopropylamine (17 mL). After stirring at room temperature for 6 h, the reaction mixture was filtered and the filtrate evaporated to dryness. The product was purified by column chromatography on silica using dichloromethane/THF (10:1) as eluent to give 200 mg (71%) of (E)(E) 2,7-bis-(5-hydroxy-3-methyl-pent-3-en-1-ynyl)-fluoren-9-one.

Provenance & Evidence